circumdatin H (CHEBI:65634)

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ChEBI Name	circumdatin H

ChEBI ID	CHEBI:65634

Definition	An organic heteropentacyclic compound that is 5b,7,8,16-tetrahydro-6H,10H-pyrrolo[2,1-c]quinazolino[3,2-a][1,4]benzodiazepine substituted by a methoxy group at position 2 and oxo groups at positions 10 and 16 (the 5bS stereoisomer). An alkaloid isolated from the culture broth of Aspergillus ochraceus, it exhibits potent inhibitory activity towards mitochondrial NADH oxidase.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

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Formula

C20H17N3O3

Net Charge

Average Mass

347.36730

Monoisotopic Mass

347.12699

InChI

InChI=1S/C20H17N3O3/c1-26-12-8-9-15-14(11-12)20(25)23-16-6-3-2-5-13(16)19(24)22-10-4-7-17(22)18(23)21-15/h2-3,5-6,8-9,11,17H,4,7,10H2,1H3/t17-/m0/s1

InChIKey

MLEAYJRUKNTODR-KRWDZBQOSA-N

SMILES

[H][C@@]12CCCN1C(=O)c1ccccc1-n1c2nc2ccc(OC)cc2c1=O

Metabolite of Species	Details
Aspergillus ochraceus (NCBI:txid40380)	See: PubMed

Roles Classification
Biological Role(s):	Aspergillus metabolite Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus . metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via alkaloid ) EC 1.6.* (oxidoreductase acting on NADH or NADPH) inhibitor An oxidoreductase inhibitor which interferes with the action of an oxidoreductase acting on NADH or NADPH (EC 1.6..).

ChEBI Ontology
Outgoing	circumdatin H (CHEBI:65634) has role Aspergillus metabolite (CHEBI:76956) circumdatin H (CHEBI:65634) has role EC 1.6.* (oxidoreductase acting on NADH or NADPH) inhibitor (CHEBI:76733) circumdatin H (CHEBI:65634) has role metabolite (CHEBI:25212) circumdatin H (CHEBI:65634) is a alkaloid (CHEBI:22315) circumdatin H (CHEBI:65634) is a aromatic ether (CHEBI:35618) circumdatin H (CHEBI:65634) is a lactam (CHEBI:24995) circumdatin H (CHEBI:65634) is a organic heteropentacyclic compound (CHEBI:38164)

IUPAC Name

(5bS)-2-methoxy-5b,6,7,8-tetrahydro-10H,16H-pyrrolo[2,1-c]quinazolino[3,2-a][1,4]benzodiazepine-10,16-dione

Synonym	Source
(S)-(−)-circumdatin H	ChEBI

Registry Number	Type	Source
15854665	Reaxys Registry Number	Reaxys

Last Modified

27 October 2016